NO773188L - Ethylenglycolprosess. - Google Patents

Ethylenglycolprosess.

Info

Publication number: NO773188L
Authority: NO; Norway
Prior art keywords: reaction; ethylene glycol; glycolaldehyde; rhodium; hydrogenation
Prior art date: 1976-09-17

Application number

NO773188A

Other languages

English (en)

Norwegian (no)

Inventor

Richard Walter Goetz

Original Assignee

Nat Distillers Chem Corp

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.)

1976-09-17

Filing date

1977-09-16

Publication date

1978-03-20

1977-09-16 Application filed by Nat Distillers Chem Corp filed Critical Nat Distillers Chem Corp

1978-03-20 Publication of NO773188L publication Critical patent/NO773188L/no

Links

LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 351
238000000034 method Methods 0.000 title claims description 71
230000008569 process Effects 0.000 title claims description 27
238000006243 chemical reaction Methods 0.000 claims description 118
WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 116
239000003054 catalyst Substances 0.000 claims description 71
239000010948 rhodium Substances 0.000 claims description 52
229910052703 rhodium Inorganic materials 0.000 claims description 42
238000005984 hydrogenation reaction Methods 0.000 claims description 40
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 38
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 38
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 30
229910002091 carbon monoxide Inorganic materials 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 30
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 26
239000011541 reaction mixture Substances 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 14
150000001408 amides Chemical class 0.000 claims description 11
230000015572 biosynthetic process Effects 0.000 claims description 9
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 6
239000007810 chemical reaction solvent Substances 0.000 claims description 5
230000003301 hydrolyzing effect Effects 0.000 claims description 4
AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims description 4
150000003857 carboxamides Chemical class 0.000 claims description 2
239000011260 aqueous acid Substances 0.000 claims 2
GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 193
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 81
239000000047 product Substances 0.000 description 45
239000002904 solvent Substances 0.000 description 44
238000004458 analytical method Methods 0.000 description 31
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
238000004519 manufacturing process Methods 0.000 description 27
239000000203 mixture Substances 0.000 description 23
239000000243 solution Substances 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
150000001412 amines Chemical class 0.000 description 15
-1 cyclic acetals Chemical class 0.000 description 15
239000007789 gas Substances 0.000 description 15
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 13
239000007795 chemical reaction product Substances 0.000 description 13
238000006460 hydrolysis reaction Methods 0.000 description 13
239000003446 ligand Substances 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
229930040373 Paraformaldehyde Natural products 0.000 description 12
230000007062 hydrolysis Effects 0.000 description 12
229920002866 paraformaldehyde Polymers 0.000 description 12
238000006722 reduction reaction Methods 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 11
235000011054 acetic acid Nutrition 0.000 description 11
229920005862 polyol Polymers 0.000 description 11
150000003077 polyols Chemical class 0.000 description 11
230000009467 reduction Effects 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
230000035484 reaction time Effects 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
150000001241 acetals Chemical class 0.000 description 9
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
150000001299 aldehydes Chemical class 0.000 description 8
229910052763 palladium Inorganic materials 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
239000006227 byproduct Substances 0.000 description 5
229910017052 cobalt Inorganic materials 0.000 description 5
239000010941 cobalt Substances 0.000 description 5
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000004821 distillation Methods 0.000 description 5
235000019441 ethanol Nutrition 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
229910052759 nickel Inorganic materials 0.000 description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
238000009835 boiling Methods 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000013110 organic ligand Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical class C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
230000008859 change Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000004508 fractional distillation Methods 0.000 description 3
238000001030 gas--liquid chromatography Methods 0.000 description 3
125000001183 hydrocarbyl group Chemical group 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000011084 recovery Methods 0.000 description 3
238000011946 reduction process Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical class C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000013022 venting Methods 0.000 description 3
ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical class COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 3
FILVIKOEJGORQS-UHFFFAOYSA-N 1,5-dimethylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C FILVIKOEJGORQS-UHFFFAOYSA-N 0.000 description 2
ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 2
LVUQCTGSDJLWCE-UHFFFAOYSA-N 1-benzylpyrrolidin-2-one Chemical compound O=C1CCCN1CC1=CC=CC=C1 LVUQCTGSDJLWCE-UHFFFAOYSA-N 0.000 description 2
GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 2
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
230000008901 benefit Effects 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
238000010960 commercial process Methods 0.000 description 2
239000006184 cosolvent Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000007423 decrease Effects 0.000 description 2
BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical class CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
239000011521 glass Substances 0.000 description 2
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
150000002373 hemiacetals Chemical class 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
239000000463 material Substances 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
150000004885 piperazines Chemical class 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
125000000075 primary alcohol group Chemical group 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
239000003586 protic polar solvent Substances 0.000 description 2
150000003284 rhodium compounds Chemical class 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
229910052814 silicon oxide Inorganic materials 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000007039 two-step reaction Methods 0.000 description 2
POILWHVDKZOXJZ-ONEGZZNKSA-M (E)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C/C(C)=O POILWHVDKZOXJZ-ONEGZZNKSA-M 0.000 description 1
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
229910021536 Zeolite Inorganic materials 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000003869 acetamides Chemical class 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
150000003927 aminopyridines Chemical class 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
230000002528 anti-freeze Effects 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001495 arsenic compounds Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
SZQABOJVTZVBHE-UHFFFAOYSA-N carbon monoxide;rhodium Chemical group [Rh].[Rh].[Rh].[Rh].[Rh].[Rh].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] SZQABOJVTZVBHE-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000003245 coal Substances 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
239000002826 coolant Substances 0.000 description 1
239000010949 copper Substances 0.000 description 1
229910052802 copper Inorganic materials 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
238000012937 correction Methods 0.000 description 1
150000003950 cyclic amides Chemical class 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940015043 glyoxal Drugs 0.000 description 1
229940093920 gynecological arsenic compound Drugs 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
150000005217 methyl ethers Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
YKOQQFDCCBKROY-UHFFFAOYSA-N n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)CC YKOQQFDCCBKROY-UHFFFAOYSA-N 0.000 description 1
MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
238000005457 optimization Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000010355 oscillation Effects 0.000 description 1
SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
150000004672 propanoic acids Chemical class 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003233 pyrroles Chemical class 0.000 description 1
150000003235 pyrrolidines Chemical class 0.000 description 1
150000004040 pyrrolidinones Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003283 rhodium Chemical class 0.000 description 1
229910003450 rhodium oxide Inorganic materials 0.000 description 1
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000009469 supplementation Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical class OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups
- 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
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials

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)

NO773188A 1976-09-17 1977-09-16 Ethylenglycolprosess. NO773188L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US72412676A	1976-09-17	1976-09-17

Publications (1)

Publication Number	Publication Date
NO773188L true NO773188L (no)	1978-03-20

Family

ID=24909126

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO773188A NO773188L (no)	1976-09-17	1977-09-16	Ethylenglycolprosess.

Country Status (16)

Country	Link
JP (2)	JPS5337606A (it)
BE (1)	BE858806A (it)
BR (1)	BR7706226A (it)
CA (1)	CA1089877A (it)
DE (1)	DE2741589C2 (it)
DK (1)	DK411477A (it)
ES (1)	ES462430A1 (it)
FI (1)	FI772720A (it)
FR (1)	FR2363538A1 (it)
GB (1)	GB1585604A (it)
IE (1)	IE45512B1 (it)
IT (1)	IT1086478B (it)
LU (1)	LU78137A1 (it)
MX (1)	MX146305A (it)
NL (1)	NL7710187A (it)
NO (1)	NO773188L (it)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1089876A (en) *	1976-10-21	1980-11-18	Robert G. Wall	Alcohol production
DE2861830D1 (en) *	1977-12-16	1982-07-01	Monsanto Co	Hydroformylation of formaldehyde with rhodium catalyst
US4317946A (en)	1980-06-27	1982-03-02	The Halcon Sd Group, Inc.	Process for producing ethylene glycol via catalytic hydrogenation of glycolaldehyde
US4321414A (en) *	1980-08-26	1982-03-23	The Halcon Sd Group, Inc.	Catalytic hydrogenation of glycolaldehyde to produce ethylene glycol
US4382148A (en) *	1981-03-24	1983-05-03	Shell Oil Company	Process for the preparation of glycol aldehyde
US4414421A (en) *	1981-08-03	1983-11-08	Shell Oil Company	Process for the preparation of glycol aldehyde
US4496781A (en) *	1984-04-05	1985-01-29	The Halcon Sd Group, Inc.	Process for the production of ethylene glycol through the hydroformylation of glycol aldehyde
US7420093B2 (en)	2006-09-29	2008-09-02	Eastman Chemical Company	Process for the preparation of glycolaldehyde

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2451333A (en) *	1945-04-28	1948-10-12	Du Pont	Synthesis of polyhydroxy compounds
JPS521821B2 (it) *	1971-09-23	1977-01-18
US3833634A (en) *	1971-12-21	1974-09-03	Union Carbide Corp	Manufacture of polyfunctional compounds
JPS5615935B2 (it) *	1973-05-31	1981-04-13
JPS5243812B2 (it) *	1973-06-12	1977-11-02
CA1089876A (en) *	1976-10-21	1980-11-18	Robert G. Wall	Alcohol production

1977
- 1977-09-12 IE IE1874/77A patent/IE45512B1/en unknown
- 1977-09-13 CA CA286,604A patent/CA1089877A/en not_active Expired
- 1977-09-13 GB GB38186/77A patent/GB1585604A/en not_active Expired
- 1977-09-14 MX MX170576A patent/MX146305A/es unknown
- 1977-09-15 DE DE2741589A patent/DE2741589C2/de not_active Expired
- 1977-09-15 FI FI772720A patent/FI772720A/fi not_active Application Discontinuation
- 1977-09-15 FR FR7727928A patent/FR2363538A1/fr active Granted
- 1977-09-16 ES ES462430A patent/ES462430A1/es not_active Expired
- 1977-09-16 BR BR7706226A patent/BR7706226A/pt unknown
- 1977-09-16 DK DK411477A patent/DK411477A/da not_active Application Discontinuation
- 1977-09-16 NL NL7710187A patent/NL7710187A/xx not_active Application Discontinuation
- 1977-09-16 IT IT27632/77A patent/IT1086478B/it active
- 1977-09-16 NO NO773188A patent/NO773188L/no unknown
- 1977-09-16 JP JP11060877A patent/JPS5337606A/ja active Granted
- 1977-09-16 BE BE180996A patent/BE858806A/xx unknown
- 1977-09-16 LU LU78137A patent/LU78137A1/xx unknown
1986
- 1986-09-17 JP JP61217332A patent/JPS62116536A/ja active Granted

Also Published As

Publication number	Publication date
MX146305A (es)	1982-06-03
FI772720A (fi)	1978-03-18
GB1585604A (en)	1981-03-11
NL7710187A (nl)	1978-03-21
LU78137A1 (it)	1978-06-01
JPS62116536A (ja)	1987-05-28
DE2741589C2 (de)	1986-10-23
JPS5337606A (en)	1978-04-06
DE2741589A1 (de)	1978-03-23
DK411477A (da)	1978-03-18
IE45512B1 (en)	1982-09-08
ES462430A1 (es)	1978-06-01
JPH0132214B2 (it)	1989-06-29
BE858806A (fr)	1978-03-16
IT1086478B (it)	1985-05-28
JPS627177B2 (it)	1987-02-16
BR7706226A (pt)	1978-07-04
FR2363538A1 (fr)	1978-03-31
FR2363538B1 (it)	1983-11-18
IE45512L (en)	1978-03-17
CA1089877A (en)	1980-11-18

Publication	Publication Date	Title
US4200765A (en)	1980-04-29	Glycol aldehyde and ethylene glycol processes
US4514521A (en)	1985-04-30	Manufacture of oxygenated compounds
US4429056A (en)	1984-01-31	Manufacture of oxygenated compounds
JP2008515843A (ja)	2008-05-15	光学活性カルボニル化合物の製造方法
AU2004293237A1 (en)	2005-06-09	Hydrogenolysis of sugar feedstock
EP0002908A1 (en)	1979-07-11	Hydroformylation of formaldehyde with rhodium catalyst
NO773188L (no)	1978-03-20	Ethylenglycolprosess.
KR101127019B1 (ko)	2012-03-26	락탐의 제조방법
WO2005068408A1 (en)	2005-07-28	Methods for preparing 1,3-butylene glycol
US4405821A (en)	1983-09-20	Process for preparing glycolaldehyde and/or ethylene glycol
US4620949A (en)	1986-11-04	Process for amidocarbonylation of cyclic amides
EP1123270A1 (en)	2001-08-16	Preparation of amines
US4291179A (en)	1981-09-22	Rhodium catalyzed process for acetaldehyde and ethanol
USRE32084E (en)	1986-02-18	Glycol aldehyde and ethylene glycol processes
CA1173059A (en)	1984-08-21	Manufacture of oxygenated compounds
CN112225655B (zh)	2024-02-27	一种柠檬醛的制备方法
US4414421A (en)	1983-11-08	Process for the preparation of glycol aldehyde
NO310612B1 (no)	2001-07-30	Fremgangsmåte for fremstilling av 1,3-alkandioler
CA1309108C (en)	1992-10-20	Hydroformylation of aqueous formaldehyde using a rhodium-tricyclohexylphosphine catalyst system
EP0170830A1 (en)	1986-02-12	A process for amido carbonylation of an aldehyde to n-acetyl alpha-amino acids
JP2007510638A (ja)	2007-04-26	ジカルボン酸および／またはその酸無水物の水素化の均一系方法
EP0039061A1 (en)	1981-11-04	Preparation of amines from olefins using certain transition metal catalysts
US4482647A (en)	1984-11-13	Manufacture of oxygenated compounds
JP3882245B2 (ja)	2007-02-14	フィトン及びイソフィトールの製造方法
US4001336A (en)	1977-01-04	2,6,10-trimethyl-dodecan-1-al and 2,6,10-trimethyl-dodeca-4,8-dien-1-al