DE2033656A1 - Verfahren zur Herstellung von Dihydroxybenzolen und deren Carbon sauree stern - Google Patents

Verfahren zur Herstellung von Dihydroxybenzolen und deren Carbon sauree stern

Info

Publication number: DE2033656A1
Authority: DE; Germany
Prior art keywords: oxygen; cyclohexenyl; reaction; carboxylate; carboxylic acid
Prior art date: 1969-07-07
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.): Pending

Application number

DE19702033656

Other languages

German (de)

English (en)

Inventor

Martin Barry Bergen Sugerman Gerald Morns NJ Sherwin (V St A )

Original Assignee

Chem Systems, Ine , New York, N \ (V St A)

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.)

1969-07-07

Filing date

1970-07-07

Publication date

1971-01-21

1970-07-07 Application filed by Chem Systems, Ine , New York, N \ (V St A) filed Critical Chem Systems, Ine , New York, N \ (V St A)

1971-01-21 Publication of DE2033656A1 publication Critical patent/DE2033656A1/de

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 37
238000004519 manufacturing process Methods 0.000 title claims description 9
150000005205 dihydroxybenzenes Chemical class 0.000 title description 9
230000002378 acidificating effect Effects 0.000 title description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title description 2
229910052799 carbon Inorganic materials 0.000 title description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 25
239000003054 catalyst Substances 0.000 claims description 20
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 claims description 12
239000007789 gas Substances 0.000 claims description 11
DRJNNZMCOCQJGI-UHFFFAOYSA-N cyclohexen-1-yl acetate Chemical compound CC(=O)OC1=CCCCC1 DRJNNZMCOCQJGI-UHFFFAOYSA-N 0.000 claims description 8
150000001733 carboxylic acid esters Chemical class 0.000 claims description 7
229910017052 cobalt Inorganic materials 0.000 claims description 7
239000010941 cobalt Substances 0.000 claims description 7
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 7
150000007942 carboxylates Chemical class 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
229910052750 molybdenum Inorganic materials 0.000 claims description 5
229910052720 vanadium Inorganic materials 0.000 claims description 5
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 4
229910001385 heavy metal Inorganic materials 0.000 claims description 4
239000011733 molybdenum Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
-1 cyclohexenyl compound Chemical class 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
150000008065 acid anhydrides Chemical class 0.000 claims description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 1
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 24
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 20
238000007254 oxidation reaction Methods 0.000 description 19
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 17
230000003647 oxidation Effects 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
238000006356 dehydrogenation reaction Methods 0.000 description 12
239000002243 precursor Substances 0.000 description 12
239000000126 substance Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
239000000047 product Substances 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000012808 vapor phase Substances 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
230000018044 dehydration Effects 0.000 description 4
238000006297 dehydration reaction Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000007791 liquid phase Substances 0.000 description 4
125000005609 naphthenate group Chemical group 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
238000010533 azeotropic distillation Methods 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000243 solution Substances 0.000 description 3
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 3
GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
238000006701 autoxidation reaction Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
SQZNAONOTRQTIE-UHFFFAOYSA-N cyclohexen-1-yl propanoate Chemical compound CCC(=O)OC1=CCCCC1 SQZNAONOTRQTIE-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
150000002561 ketenes Chemical class 0.000 description 2
238000011068 loading method Methods 0.000 description 2
229910052748 manganese Inorganic materials 0.000 description 2
239000011572 manganese Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
238000005502 peroxidation Methods 0.000 description 2
238000010791 quenching Methods 0.000 description 2
230000000171 quenching effect Effects 0.000 description 2
239000002994 raw material Substances 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
FBSAITBEAPNWJG-UHFFFAOYSA-N (2-acetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
STOUHHBZBQBYHH-UHFFFAOYSA-N (3-acetyloxyphenyl) acetate Chemical compound CC(=O)OC1=CC=CC(OC(C)=O)=C1 STOUHHBZBQBYHH-UHFFFAOYSA-N 0.000 description 1
UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 description 1
ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 1
VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 description 1
GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
229920013683 Celanese Polymers 0.000 description 1
YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
101001094044 Mus musculus Solute carrier family 26 member 6 Proteins 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 description 1
239000003139 biocide Substances 0.000 description 1
230000002599 biostatic effect Effects 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
235000012255 calcium oxide Nutrition 0.000 description 1
150000004651 carbonic acid esters Chemical class 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical class O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
UCAOXQAUNJVPOZ-UHFFFAOYSA-N cyclohexen-1-yl butanoate Chemical compound CCCC(=O)OC1=CCCCC1 UCAOXQAUNJVPOZ-UHFFFAOYSA-N 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000003804 extraction from natural source Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000005171 halobenzenes Chemical class 0.000 description 1
239000000383 hazardous chemical Substances 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical class CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910052758 niobium Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
238000003822 preparative gas chromatography Methods 0.000 description 1
238000000197 pyrolysis Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
229910052714 tellurium Inorganic materials 0.000 description 1
239000004753 textile Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
150000005691 triesters Chemical class 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions decreasing the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals

Landscapes

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

DE19702033656 1969-07-07 1970-07-07 Verfahren zur Herstellung von Dihydroxybenzolen und deren Carbon sauree stern Pending DE2033656A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US83970169A	1969-07-07	1969-07-07

Publications (1)

Publication Number	Publication Date
DE2033656A1 true DE2033656A1 (de)	1971-01-21

Family

ID=25280435

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19702033656 Pending DE2033656A1 (de)	1969-07-07	1970-07-07	Verfahren zur Herstellung von Dihydroxybenzolen und deren Carbon sauree stern

Country Status (6)

Country	Link
BE (1)	BE753034A (fr)
DE (1)	DE2033656A1 (fr)
ES (1)	ES381514A1 (fr)
FR (1)	FR2054212A5 (fr)
LU (1)	LU61262A1 (fr)
NL (1)	NL7009937A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0060381A1 (fr) *	1981-03-12	1982-09-22	Hüls Aktiengesellschaft	Procédé pour la préparation de 3,3-diméthyl-2-alcoxyoxirannes par oxydation de 1-alcoxy-2-méthylpropène

1970
- 1970-07-03 LU LU61262D patent/LU61262A1/xx unknown
- 1970-07-04 NL NL7009937A patent/NL7009937A/xx unknown
- 1970-07-06 FR FR7024972A patent/FR2054212A5/fr not_active Expired
- 1970-07-06 BE BE753034D patent/BE753034A/fr unknown
- 1970-07-07 ES ES381514A patent/ES381514A1/es not_active Expired
- 1970-07-07 DE DE19702033656 patent/DE2033656A1/de active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0060381A1 (fr) *	1981-03-12	1982-09-22	Hüls Aktiengesellschaft	Procédé pour la préparation de 3,3-diméthyl-2-alcoxyoxirannes par oxydation de 1-alcoxy-2-méthylpropène

Also Published As

Publication number	Publication date
FR2054212A5 (en)	1971-04-16
LU61262A1 (fr)	1971-09-22
ES381514A1 (es)	1972-10-16
BE753034A (fr)	1971-01-06
NL7009937A (fr)	1971-01-11

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DE1281426B (de)	1969-04-30	Verfahren zur Herstellung von 2, 6-Di-tertiaer-butyl-hydrochinon
EP0257243B1 (fr)	1991-10-23	Procédé de préparation de diols vicinaux
EP0322660B1 (fr)	1991-08-28	Procédé pour la séparation de méthyl-2 butanal
EP0700892B1 (fr)	1999-03-24	Procédé de préparation d'acides mono- ou dicarboxyliques à partir des aldéhydes, leurs acétals ou hemi-acétals, comme aussi à partir de leurs mélanges
DE2411440C3 (fr)	1978-08-17
DE1196646B (de)	1965-07-15	Verfahren zur Herstellung von Cyclododecanol
DE2033656A1 (de)	1971-01-21	Verfahren zur Herstellung von Dihydroxybenzolen und deren Carbon sauree stern
DE2601537C2 (de)	1984-10-18	Verfahren zur Herstellung von Formiatestern alkylsubstituierter aromatischer Hydroxyverbindungen
DE4104419A1 (de)	1992-08-20	Kreislaufverfahren zur herstellung von cyclohexenoxid sowie cyclohexanol und cyclohexanon
US3462481A (en)	1969-08-19	Method of production of unsaturated acids
DE1518970C3 (de)	1976-09-02	Verfahren zur Herstellung von gesättigten aliphatischen Dicarbonsäuren
DE1914572B2 (de)	1978-09-21	Verfahren zur Herstellung von Dodecandisäure -1,12
DE1299624B (de)	1969-07-24	Verfahren zur Herstellung von Adipinsaeure
DE2513678C3 (de)	1978-05-18	Verfahren zur Herstellung von praktisch ameisensäurefreier Essigsäure
DE2225450C3 (de)	1980-03-20	Verfahren zur gleichzeitigen Herstellung von Propylenoxid und Essigsäure
DE1111177B (de)	1961-07-20	Verfahren zur Herstellung von Cyclododecanon und Cyclododecanol
AT202558B (de)	1959-03-10	Verfahren zur Herstellung aliphatischer Permonocarbonsäuren
DE1643985C3 (de)	1975-02-20	S-lsopropyl^nitro-phenyl-dimethyl-carbinol und 3,5-Diisopropyl-4-nitro-phenyldimethylcarbinol und Verfahren zu deren Herstellung
DE2609566C3 (de)	1979-05-23	Verfahren zur Herstellung von Methylheptenon
DE1518261C3 (fr)	1974-09-26
DE2150294A1 (de)	1973-04-12	Verfahren zur herstellung von 2-cyclohexenon
DE1518970B2 (de)	1976-01-15	Verfahren zur herstellung von gesaettigten aliphatischen dicarbonsaeuren
DE1293142B (de)	1969-04-24	Verfahren zur Herstellung von Olefinoxiden sowie Isobuttersaeure

DE2033656A1 - Verfahren zur Herstellung von Dihydroxybenzolen und deren Carbon sauree stern - Google Patents

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