CA1249837A - Methode de preparation de butanediol-1,4 - Google Patents

Methode de preparation de butanediol-1,4

Info

Publication number: CA1249837A
Authority: CA; Canada
Prior art keywords: hydrogenolysis; ester; vaporous; butane; diol
Prior art date: 1984-11-21
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

CA000495906A

Other languages

English (en)

Inventor

John W. Kippax

Keith Turner

Mohammad Sharif

Colin Rathmell

John Scarlett

Arthur J. Reason

Norman Harris

Anthony B. Carter

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.)

Johnson Matthey Davy Technologies Ltd

Original Assignee

Davy Mckee London Ltd

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.)

1984-11-21

Filing date

1985-11-21

Publication date

1989-02-07

1984-11-21 Priority claimed from US06/673,797 external-priority patent/US4584419A/en

1985-06-04 Priority claimed from GB858514002A external-priority patent/GB8514002D0/en

1985-11-21 Application filed by Davy Mckee London Ltd filed Critical Davy Mckee London Ltd

1989-02-07 Application granted granted Critical

1989-02-07 Publication of CA1249837A publication Critical patent/CA1249837A/fr

Status Expired legal-status Critical Current

Links

WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 title claims abstract description 104
238000000034 method Methods 0.000 title claims abstract description 40
238000004519 manufacturing process Methods 0.000 title claims abstract description 19
238000007327 hydrogenolysis reaction Methods 0.000 claims abstract description 87
150000002148 esters Chemical class 0.000 claims abstract description 79
239000003054 catalyst Substances 0.000 claims abstract description 56
239000000203 mixture Substances 0.000 claims abstract description 43
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims abstract description 40
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 38
IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 claims abstract description 19
IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims abstract description 19
238000006243 chemical reaction Methods 0.000 claims abstract description 18
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 30
239000011541 reaction mixture Substances 0.000 claims description 29
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
239000007788 liquid Substances 0.000 claims description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical group CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 claims description 17
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 6
229910052804 chromium Inorganic materials 0.000 claims description 6
239000011651 chromium Substances 0.000 claims description 6
239000010949 copper Substances 0.000 claims description 6
229910052802 copper Inorganic materials 0.000 claims description 6
230000018044 dehydration Effects 0.000 claims description 6
238000006297 dehydration reaction Methods 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
238000001816 cooling Methods 0.000 claims description 4
IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 abstract description 40
238000011144 upstream manufacturing Methods 0.000 abstract description 16
-1 diethyl maleate Chemical compound 0.000 abstract description 15
TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 abstract description 3
229910017518 Cu Zn Inorganic materials 0.000 abstract 1
229910017752 Cu-Zn Inorganic materials 0.000 abstract 1
229910017813 Cu—Cr Inorganic materials 0.000 abstract 1
229910017943 Cu—Zn Inorganic materials 0.000 abstract 1
125000005907 alkyl ester group Chemical group 0.000 abstract 1
INDXRDWMTVLQID-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO.OCCCCO INDXRDWMTVLQID-UHFFFAOYSA-N 0.000 abstract 1
239000000047 product Substances 0.000 description 27
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 20
239000007789 gas Substances 0.000 description 17
238000011027 product recovery Methods 0.000 description 15
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 12
239000006227 byproduct Substances 0.000 description 11
239000012071 phase Substances 0.000 description 11
229930188620 butyrolactone Natural products 0.000 description 10
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 9
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 8
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
239000011261 inert gas Substances 0.000 description 7
239000011976 maleic acid Substances 0.000 description 7
239000000463 material Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000007791 liquid phase Substances 0.000 description 5
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
238000010926 purge Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000005751 Copper oxide Substances 0.000 description 4
125000005233 alkylalcohol group Chemical group 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
229910000431 copper oxide Inorganic materials 0.000 description 4
229960004643 cupric oxide Drugs 0.000 description 4
238000004821 distillation Methods 0.000 description 4
235000011087 fumaric acid Nutrition 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000007921 spray Substances 0.000 description 4
235000011044 succinic acid Nutrition 0.000 description 4
229910001868 water Inorganic materials 0.000 description 4
239000011787 zinc oxide Substances 0.000 description 4
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
238000002203 pretreatment Methods 0.000 description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
239000001384 succinic acid Substances 0.000 description 3
229940014800 succinic anhydride Drugs 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
229910002477 CuCr2O4 Inorganic materials 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000001273 butane Substances 0.000 description 2
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
FULFYAFFAGNFJM-UHFFFAOYSA-N oxocopper;oxo(oxochromiooxy)chromium Chemical compound [Cu]=O.O=[Cr]O[Cr]=O FULFYAFFAGNFJM-UHFFFAOYSA-N 0.000 description 2
238000004064 recycling Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
FHVRTMVXBVDWCK-UHFFFAOYSA-N 2-methyl-2-prop-2-enoxypropane Chemical compound CC(C)(C)OCC=C FHVRTMVXBVDWCK-UHFFFAOYSA-N 0.000 description 1
ZJVRXWVVJPAKGP-UHFFFAOYSA-N 4-[(2-methylpropan-2-yl)oxy]butanal Chemical compound CC(C)(C)OCCCC=O ZJVRXWVVJPAKGP-UHFFFAOYSA-N 0.000 description 1
OGYSYXDNLPNNPW-UHFFFAOYSA-N 4-butoxy-4-oxobutanoic acid Chemical compound CCCCOC(=O)CCC(O)=O OGYSYXDNLPNNPW-UHFFFAOYSA-N 0.000 description 1
238000004438 BET method Methods 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
229910002528 Cu-Pd Inorganic materials 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
238000005602 Reppe reaction Methods 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
LRFQSNDOLFTQCR-UHFFFAOYSA-M [O-][Cr](O)(=O)=O.N.[Cu+] Chemical compound [O-][Cr](O)(=O)=O.N.[Cu+] LRFQSNDOLFTQCR-UHFFFAOYSA-M 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical compound O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
229940001007 aluminium phosphate Drugs 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000001174 ascending effect Effects 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
WERYXYBDKMZEQL-CQDYUVAPSA-N butane-1,4-diol Chemical group O[13CH2]CC[13CH2]O WERYXYBDKMZEQL-CQDYUVAPSA-N 0.000 description 1
229910002090 carbon oxide Inorganic materials 0.000 description 1
238000003889 chemical engineering Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000010276 construction Methods 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
CFQJFBMLIAGCOU-UHFFFAOYSA-N copper;chromium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Cr+3].[Cr+3].[Cu+2] CFQJFBMLIAGCOU-UHFFFAOYSA-N 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 1
JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
GGAWXQQNQGESAW-UHFFFAOYSA-N dibutyl 2-butoxybutanedioate Chemical compound CCCCOC(=O)C(OCCCC)CC(=O)OCCCC GGAWXQQNQGESAW-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
239000000446 fuel Substances 0.000 description 1
150000002238 fumaric acids Chemical class 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000007037 hydroformylation reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229960004592 isopropanol Drugs 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
239000003863 metallic catalyst Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001707 polybutylene terephthalate Polymers 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 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
239000003507 refrigerant Substances 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
229940007718 zinc hydroxide Drugs 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
- C07C29/147—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 carboxylic acids or derivatives thereof
- C07C29/149—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 carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
- 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
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/177—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of a carboxy group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000495906A 1984-11-21 1985-11-21 Methode de preparation de butanediol-1,4 Expired CA1249837A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US06/673,797 US4584419A (en)	1983-11-29	1984-11-21	Process for the production of butane-1,4-diol
US673,797		1984-11-21
GB8514002		1985-06-04
GB858514002A GB8514002D0 (en)	1985-06-04	1985-06-04	Process

Publications (1)

Publication Number	Publication Date
CA1249837A true CA1249837A (fr)	1989-02-07

Family

ID=26289326

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000495906A Expired CA1249837A (fr)	1984-11-21	1985-11-21	Methode de preparation de butanediol-1,4

Country Status (6)

Country	Link
EP (1)	EP0204730A1 (fr)
JP (1)	JPH0655684B2 (fr)
BR (1)	BR8507068A (fr)
CA (1)	CA1249837A (fr)
ES (1)	ES8701703A1 (fr)
WO (1)	WO1986003189A1 (fr)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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GB8618892D0 (en) *	1986-08-01	1986-09-10	Davy Mckee Ltd	Process
WO1988000937A1 (fr) *	1986-08-01	1988-02-11	Davy Mckee (London) Limited	Procede pour la coproduction de butane-1,4-diol et de gamma-butyrolactone
GB8717993D0 (en) *	1987-07-29	1987-09-03	Davy Mckee Ltd	Process
GB8717989D0 (en) *	1987-07-29	1987-09-03	Davy Mckee Ltd	Catalyst
US4810807A (en) *	1987-10-13	1989-03-07	The Standard Oil Company	Hydrogenation of maleic anhydride to tetrahydrofuran
JPH02233674A (ja) *	1989-03-07	1990-09-17	Mitsubishi Kasei Corp	ラクトン類の製造法
GB8917862D0 (en) *	1989-08-04	1989-09-20	Davy Mckee London	Process
GB8917859D0 (en) *	1989-08-04	1989-09-20	Davy Mckee London	Process
GB8917864D0 (en) *	1989-08-04	1989-09-20	Davy Mckee London	Process
DE4005293A1 (de) *	1990-02-20	1991-08-22	Basf Ag	Verfahren zur herstellung von tetrahydrofuran und -butyrolacton
DE4231782A1 (de) *	1992-09-23	1994-03-24	Basf Ag	Verfahren zur Herstellung von 2-Methyl-1,4-butandiol und 3-Methyltetrahydrofuran
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GB9324782D0 (en) *	1993-12-02	1994-01-19	Davy Mckee London	Process
GB9324784D0 (en) *	1993-12-02	1994-01-19	Davy Mckee London	Process
GB9324823D0 (en) *	1993-12-02	1994-01-19	Davy Mckee London	Process
GB9324786D0 (en) *	1993-12-02	1994-01-19	Davy Mckee London	Process
GB9324785D0 (en) *	1993-12-02	1994-01-19	Davy Mckee London	Process
GB9324783D0 (en) *	1993-12-02	1994-01-19	Davy Mckee London	Process
GB9324753D0 (en) *	1993-12-02	1994-01-19	Davy Mckee London	Process
GB9324752D0 (en) *	1993-12-02	1994-01-19	Davy Mckee London	Process
IT1273320B (it) *	1994-02-22	1997-07-08	Alusuisse Italia Spa	Procedimento per la produzione di gamma-butirrolattone
DE4431220A1 (de) *	1994-09-02	1996-03-07	Bayer Ag	Verfahren zur Herstellung von Butandiol-1,4 aus Maleinsäureanhydrid
ZA973972B (en) *	1996-05-14	1998-03-23	Kvaerner Process Tech Ltd	A process for the production of at least one C4 compound selected from butane-1,4-diol, gamma-butyrolactone and tetrahydrofuran.
ZA973971B (en) *	1996-05-15	1998-03-23	Kvaerner Process Tech Ltd	A process for the production of at least one C4 compound selected from butane-1,4-diol, gamma-butyrolactone and tetrahydrofuran.
GB9724004D0 (en)	1997-11-13	1998-10-21	Kvaerner Process Tech Ltd	Process
GB9724195D0 (en)	1997-11-14	1998-01-14	Kvaerner Process Tech Ltd	Process
BE1011698A6 (fr)	1998-01-08	1999-12-07	Pantochim Sa	Procede de production de tetrahydrofuranne, de gamma-butyrolactone et de butanediol.
IT1298096B1 (it)	1998-01-09	1999-12-20	Lonza Spa	Procedimento per la produzione di gamma-butirrolattone
IT1298535B1 (it)	1998-02-02	2000-01-12	Lonza Spa	Procedimento per la produzione di gamma-butirrolattone
DE69800886T2 (de)	1998-03-23	2001-10-11	Basf Ag	Verfahren zur Herstellung von 1,4-Butandiol, Butyrolacton und Tetrahydrofuran
DE19842847A1 (de) *	1998-09-18	2000-03-23	Basf Ag	Verfahren zur Herstellung von Tetrahydrofuran
EP1108702A1 (fr) *	1999-12-13	2001-06-20	Kvaerner Process Technology Limited	Procédé pour la coproduction de diols aliphatiques et d'éthers cycliques
GB0117090D0 (en) *	2001-07-12	2001-09-05	Kvaerner Process Tech Ltd	Process
GB0329152D0 (en) *	2003-12-16	2004-01-21	Davy Process Techn Ltd	Process
GB0803663D0 (en)	2008-02-28	2008-04-09	Davy Process Techn Ltd	Process
GB201318175D0 (en)	2013-10-14	2013-11-27	Johnson Matthey Davy Technologies Ltd	Process
GB201321627D0 (en)	2013-12-06	2014-01-22	Johnson Matthey Davy Technologies Ltd	Process
GB201321611D0 (en)	2013-12-06	2014-01-22	Johnson Matthey Davy Technologies Ltd	Process
GB201507234D0 (en)	2015-04-28	2015-06-10	Johnson Matthey Davy Technologies Ltd	Process
CN114829347B (zh) *	2019-12-10	2025-03-18	巴斯夫欧洲公司	在避免聚合物沉积的同时在气相中生产1,4-丁二醇、γ-丁内酯和四氢呋喃的方法

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GB8331793D0 (en) *	1983-11-29	1984-01-04	Davy Mckee Ltd	Process

1985
- 1985-11-18 BR BR8507068A patent/BR8507068A/pt unknown
- 1985-11-18 WO PCT/GB1985/000524 patent/WO1986003189A1/fr not_active Ceased
- 1985-11-18 EP EP19850905648 patent/EP0204730A1/fr not_active Withdrawn
- 1985-11-18 JP JP61500083A patent/JPH0655684B2/ja not_active Expired - Lifetime
- 1985-11-21 CA CA000495906A patent/CA1249837A/fr not_active Expired
- 1985-11-21 ES ES549746A patent/ES8701703A1/es not_active Expired

Also Published As

Publication number	Publication date
EP0204730A1 (fr)	1986-12-17
JPH0655684B2 (ja)	1994-07-27
JPS62501702A (ja)	1987-07-09
BR8507068A (pt)	1987-07-14
ES549746A0 (es)	1986-12-01
ES8701703A1 (es)	1986-12-01
WO1986003189A1 (fr)	1986-06-05

Legal Events

Date	Code	Title	Description
2006-02-07	MKEX	Expiry

Publication	Publication Date	Title
CA1249837A (fr)	1989-02-07	Methode de preparation de butanediol-1,4
US4751334A (en)	1988-06-14	Process for the production of butane-1,4-diol
CA1246616A (fr)	1988-12-13	Preparation de butanediol-1,4
WO1986007358A1 (fr)	1986-12-18	Procede de production de gamma-butyrolactone
WO1988000937A1 (fr)	1988-02-11	Procede pour la coproduction de butane-1,4-diol et de gamma-butyrolactone
US5004845A (en)	1991-04-02	Hydrogenation of aldehydes
EP0485482B1 (fr)	1994-10-26	Procédé d'hydrogenation en phase gazeuse
US6426438B1 (en)	2002-07-30	Method for producing 1,6-hexanediol and 6-hydroxycaproic acid or their esters
CA1327812C (fr)	1994-03-15	Hydrogenation en phase vapeur de l'anhydride maleique en tetrahydrofurane et en gamma-butyrolactone
US5072009A (en)	1991-12-10	Vapor-phase hydrogenation of maleic anhydride to tetrahydrofuran and gamma-butyrolactone
US4656297A (en)	1987-04-07	Coproduction of butanediol and tetrahydrofuran and their subsequent separation from the reaction product mixture
AU2002314385B2 (en)	2007-09-20	Process for the production of ethers, typically THF
EP1694661B1 (fr)	2010-04-21	Procede de preparation d'ethers
AU2002314385A1 (en)	2003-05-22	Process for the production of ethers, typically THF
AU2009219875B2 (en)	2013-06-06	Process
KR100898455B1 (ko)	2009-05-21	결합된 기상 및 액상 수소화에 의한 1,4-부탄디올의 제조방법
MXPA00001667A (en)	2001-05-07	Method for producing 1,6-hexanediol