CA1070711A - Procede pour la preparation du butanediol-1,4 - Google Patents

Procede pour la preparation du butanediol-1,4

Info

Publication number: CA1070711A
Authority: CA; Canada
Prior art keywords: compounds; catalyst; palladium; butanediol; rhenium
Prior art date: 1975-05-03
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

CA251,589A

Other languages

English (en)

Inventor

Hans Fernholz

Dieter Freudenberger

Friedrich Wunder

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.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1975-05-03

Filing date

1976-04-30

Publication date

1980-01-29

1976-04-30 Application filed by Hoechst AG filed Critical Hoechst AG

1980-01-29 Application granted granted Critical

1980-01-29 Publication of CA1070711A publication Critical patent/CA1070711A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title abstract description 4
239000003054 catalyst Substances 0.000 claims abstract description 60
150000001875 compounds Chemical class 0.000 claims abstract description 27
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 21
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 21
239000011976 maleic acid Substances 0.000 claims abstract description 21
239000000203 mixture Substances 0.000 claims abstract description 21
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 35
238000000034 method Methods 0.000 claims description 26
229910052702 rhenium Inorganic materials 0.000 claims description 22
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 20
229910052763 palladium Inorganic materials 0.000 claims description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 15
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 11
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 11
239000012876 carrier material Substances 0.000 claims description 5
229910052697 platinum Inorganic materials 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
239000000377 silicon dioxide Substances 0.000 claims description 4
235000012239 silicon dioxide Nutrition 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
229910052741 iridium Inorganic materials 0.000 claims description 3
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 3
229910052703 rhodium Inorganic materials 0.000 claims description 3
239000010948 rhodium Substances 0.000 claims description 3
229910001928 zirconium oxide Inorganic materials 0.000 claims description 3
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
150000007942 carboxylates Chemical class 0.000 claims description 2
150000002823 nitrates Chemical class 0.000 claims description 2
229910052762 osmium Inorganic materials 0.000 claims description 2
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
229910052707 ruthenium Inorganic materials 0.000 claims description 2
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 2
229910010271 silicon carbide Inorganic materials 0.000 claims description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 2
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 1
229910052748 manganese Inorganic materials 0.000 claims 1
239000011572 manganese Substances 0.000 claims 1
ZCUFMDLYAMJYST-UHFFFAOYSA-N thorium dioxide Chemical compound O=[Th]=O ZCUFMDLYAMJYST-UHFFFAOYSA-N 0.000 claims 1
229910003452 thorium oxide Inorganic materials 0.000 claims 1
239000004408 titanium dioxide Substances 0.000 claims 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract description 21
239000000243 solution Substances 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
229940044600 maleic anhydride Drugs 0.000 description 20
239000001257 hydrogen Substances 0.000 description 17
229910052739 hydrogen Inorganic materials 0.000 description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
-1 polybutylene terephthalate Polymers 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 6
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
239000000047 product Substances 0.000 description 6
239000001384 succinic acid Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 5
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
229910017052 cobalt Inorganic materials 0.000 description 3
239000010941 cobalt Substances 0.000 description 3
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
150000002009 diols Chemical class 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 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
229930188620 butyrolactone Natural products 0.000 description 2
NKCVNYJQLIWBHK-UHFFFAOYSA-N carbonodiperoxoic acid Chemical compound OOC(=O)OO NKCVNYJQLIWBHK-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000007792 gaseous phase Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 2
229910003445 palladium oxide Inorganic materials 0.000 description 2
150000003282 rhenium compounds Chemical class 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
JYMWJWDJPYHTNF-UHFFFAOYSA-N 3-(1,4-dioxan-2-yl)furan-2,5-dione Chemical compound O1C(COCC1)/C/1=C/C(=O)OC1=O JYMWJWDJPYHTNF-UHFFFAOYSA-N 0.000 description 1
QSHYGLAZPRJAEZ-UHFFFAOYSA-N 4-(chloromethyl)-2-(2-methylphenyl)-1,3-thiazole Chemical compound CC1=CC=CC=C1C1=NC(CCl)=CS1 QSHYGLAZPRJAEZ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241001600451 Chromis Species 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000005595 acetylacetonate group Chemical group 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
238000009835 boiling Methods 0.000 description 1
MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
150000004648 butanoic acid derivatives Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
GOHCTCOGYKAJLZ-UHFFFAOYSA-N ctep Chemical compound CC=1N(C=2C=CC(OC(F)(F)F)=CC=2)C(C)=NC=1C#CC1=CC=NC(Cl)=C1 GOHCTCOGYKAJLZ-UHFFFAOYSA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
238000007865 diluting Methods 0.000 description 1
NLPVCCRZRNXTLT-UHFFFAOYSA-N dioxido(dioxo)molybdenum;nickel(2+) Chemical compound [Ni+2].[O-][Mo]([O-])(=O)=O NLPVCCRZRNXTLT-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
KZLHPYLCKHJIMM-UHFFFAOYSA-K iridium(3+);triacetate Chemical compound [Ir+3].CC([O-])=O.CC([O-])=O.CC([O-])=O KZLHPYLCKHJIMM-UHFFFAOYSA-K 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
QGAXAFUJMMYEPE-UHFFFAOYSA-N nickel chromate Chemical compound [Ni+2].[O-][Cr]([O-])(=O)=O QGAXAFUJMMYEPE-UHFFFAOYSA-N 0.000 description 1
UJRJCSCBZXLGKF-UHFFFAOYSA-N nickel rhenium Chemical compound [Ni].[Re] UJRJCSCBZXLGKF-UHFFFAOYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
150000002940 palladium Chemical class 0.000 description 1
150000002941 palladium compounds Chemical class 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920001281 polyalkylene Polymers 0.000 description 1
229920001707 polybutylene terephthalate Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 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
230000035484 reaction time Effects 0.000 description 1
SVOOVMQUISJERI-UHFFFAOYSA-K rhodium(3+);triacetate Chemical compound [Rh+3].CC([O-])=O.CC([O-])=O.CC([O-])=O SVOOVMQUISJERI-UHFFFAOYSA-K 0.000 description 1
OJLCQGGSMYKWEK-UHFFFAOYSA-K ruthenium(3+);triacetate Chemical compound [Ru+3].CC([O-])=O.CC([O-])=O.CC([O-])=O OJLCQGGSMYKWEK-UHFFFAOYSA-K 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052566 spinel group Inorganic materials 0.000 description 1
238000005507 spraying Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000004448 titration Methods 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
239000002699 waste material 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
- C07C29/17—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

Landscapes

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

CA251,589A 1975-05-03 1976-04-30 Procede pour la preparation du butanediol-1,4 Expired CA1070711A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19752519817 DE2519817A1 (de)	1975-05-03	1975-05-03	Verfahren zur herstellung von butandiol-(1.4)

Publications (1)

Publication Number	Publication Date
CA1070711A true CA1070711A (fr)	1980-01-29

Family

ID=5945719

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA251,589A Expired CA1070711A (fr)	1975-05-03	1976-04-30	Procede pour la preparation du butanediol-1,4

Country Status (7)

Country	Link
JP (1)	JPS51133212A (fr)
BE (1)	BE841409A (fr)
CA (1)	CA1070711A (fr)
DE (1)	DE2519817A1 (fr)
FR (1)	FR2310331A1 (fr)
GB (1)	GB1551741A (fr)
NL (1)	NL7604539A (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4550185A (en) *	1983-12-22	1985-10-29	E. I. Du Pont De Nemours And Company	Process for making tetrahydrofuran and 1,4-butanediol using Pd/Re hydrogenation catalyst
US4609636A (en) *	1983-12-22	1986-09-02	E. I. Du Pont De Nemours And Company	Pd/Re hydrogenation catalyst for making tetrahydrofuran and 1,4-butanediol
US7935834B2 (en)	2004-07-01	2011-05-03	Isp Investments Inc.	Catalysts for maleic acid hydrogenation to 1,4-butanediol
US8188320B2 (en)	2009-01-28	2012-05-29	Basf Se	Process for preparing pure cyclododecanone
CN110396072A (zh) *	2019-09-02	2019-11-01	上海欣海国际贸易有限公司	(s)-3-羟基四氢呋喃的制备方法

Families Citing this family (40)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1587198A (en) *	1976-11-23	1981-04-01	Ucb Sa	Process for the production of butane-1,4 diol and tetrahydrofuran
DE2715666A1 (de) *	1977-04-07	1978-10-12	Hoechst Ag	Verfahren zur herstellung von aethylenglykol
US4317918A (en) *	1979-11-05	1982-03-02	Sumitomo Chemical Co., Ltd.	Process for preparing alcohols
FR2527200A1 (fr) *	1982-05-24	1983-11-25	Inst Francais Du Petrole	Procede catalytique de production d'alcools par hydrogenolyse d'esters d'acides carboxyliques
GB8509530D0 (en) *	1985-04-13	1985-05-15	Bp Chem Int Ltd	Hydrogenation of carboxylic acids
US5149680A (en) *	1987-03-31	1992-09-22	The British Petroleum Company P.L.C.	Platinum group metal alloy catalysts for hydrogenation of carboxylic acids and their anhydrides to alcohols and/or esters
GB8707595D0 (en) *	1987-03-31	1987-05-07	British Petroleum Co Plc	Chemical process
GB8811009D0 (en) *	1988-05-10	1988-06-15	Bp Chem Int Ltd	Chemical process
GB8828616D0 (en) *	1988-12-07	1989-01-11	Bp Chem Int Ltd	Chemical process
JP2596604B2 (ja) *	1988-12-14	1997-04-02	東燃株式会社	１，４−ブタンジオールおよびテトラヒドロフランの製造方法
JP2666151B2 (ja) *	1988-12-14	1997-10-22	東燃株式会社	１，４−ブタンジオールの製造法
GB8917157D0 (en) *	1989-07-27	1989-09-13	Bp Chem Int Ltd	Chemical process
JP2595358B2 (ja) *	1989-12-07	1997-04-02	東燃株式会社	１，４―ブタンジオールおよびテトラヒドロフランの製造方法
DE4009029A1 (de) *	1990-03-21	1991-09-26	Basf Ag	Verfahren zur herstellung von 1,4-butandiol
DE4243722A1 (de) *	1992-12-23	1994-06-30	Basf Ag	Verfahren zur Herstellung von Polyetherglykolen
DE4325753A1 (de) *	1993-07-31	1995-02-02	Basf Ag	Verfahren zur Herstellung von 1,4-Butandiol
US5473086A (en) *	1995-01-17	1995-12-05	The Standard Oil Co.	Process for the hydrogenation of maleic acid to 1,4-butanediol
US5698749A (en) *	1995-09-06	1997-12-16	The Standard Oil Company	Catalysts for the hydrogenation of aqueous maleic acid to 1,4-butanediol
DE19631521A1 (de) *	1996-08-03	1998-02-05	Basf Ag	Verfahren zur Herstellung von 6-Aminocapronitril
DE19720657A1 (de) *	1997-05-16	1998-11-19	Basf Ag	Verfahren zur Herstellung von aliphatischen Alkoholen
US6486367B1 (en) *	1997-12-01	2002-11-26	The Standard Oil Company	Process for the hydrogenation of maleic acid to 1,4-butanediol
DE19807268A1 (de) *	1998-02-20	1999-08-26	Basf Ag	Verfahren zur Herstellung von Alkoholen
DE10009817A1 (de)	2000-03-01	2001-09-06	Basf Ag	Verfahren zur Herstellung von Alkoholen an rheniumhaltigen Aktivkohle-Trägerkatalysatoren
DE10014646A1 (de)	2000-03-24	2001-09-27	Basf Ag	Verfahren zur Herstellung von Alkoholen an rheniumhaltigen Aktivkohle-Trägerkatalysatoren
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DE10344595A1 (de)	2003-09-25	2005-05-12	Basf Ag	Verfahren zur Herstellung eines Ketons
DE10357718A1 (de)	2003-12-09	2005-07-21	Basf Ag	Verfahren zur Herstellung von Tricyclodecandialdehyd
DE102004046167A1 (de)	2004-09-23	2006-04-06	Basf Ag	Verfahren zur Reinigung und Aufkonzentrierung von Distickstoffmonoxid
DE102005032541A1 (de)	2005-07-12	2007-01-18	Basf Ag	Verfahren zur Hydrierung von aldehydhaltigen Stoffströmen
CN101479228B (zh)	2006-06-29	2012-08-22	巴斯夫欧洲公司	提纯环酮的方法
US7649119B2 (en)	2006-06-29	2010-01-19	Basf Se	Method for the production of cyclic ketones
ES2363614T3 (es)	2006-06-29	2011-08-10	Basf Se	Procedimiento para la purificación de cetonas cíclica.
ES2346098T3 (es)	2006-06-29	2010-10-08	Basf Se	Procedimiento para la obtencion de cetonas ciclicas.
EP2046702B1 (fr)	2006-07-25	2009-12-09	Basf Se	Procédé de reconditionnement de produits d'hydrogénation contenant un solvant
US8563781B2 (en)	2010-10-07	2013-10-22	Basf Se	Process for preparing ketones, in particular macrocyclic ketones
JP5824056B2 (ja)	2010-10-07	2015-11-25	ビーエーエスエフソシエタス・ヨーロピアＢａｓｆＳｅ	ケトン、特に大環状ケトンを調製する方法
GB201318175D0 (en)	2013-10-14	2013-11-27	Johnson Matthey Davy Technologies Ltd	Process
CN116060025B (zh) *	2021-10-31	2024-05-31	中国石油化工股份有限公司	一种加氢催化剂及其制备方法和应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2772293A (en) *	1953-07-13	1956-11-27	Du Pont	Process of hydrogenating maleic anhydride with a nickel or cobalt molybdite catalyst
US2772291A (en) *	1953-08-31	1956-11-27	Du Pont	Hydrogenation of maleic anhydride
DE1188572B (de) *	1960-05-18	1965-03-11	Basf Ag	Verfahren zur Herstellung von Alkoholen durch Hydrieren von Carbonsaeuren
DE2348353A1 (de) *	1973-09-26	1975-04-03	Bayer Ag	Verfahren zur herstellung von 2-methylpropandiol-(1,3)
DE2605107C3 (de) *	1976-02-10	1983-12-29	Chemische Werke Hüls AG, 4370 Marl	Verfahren zur Herstellung von Diolen durch katalytische Hydrierung der entsprechenden Dicarbonsäuren

1975
- 1975-05-03 DE DE19752519817 patent/DE2519817A1/de active Pending
1976
- 1976-04-28 NL NL7604539A patent/NL7604539A/xx not_active Application Discontinuation
- 1976-04-30 GB GB1771576A patent/GB1551741A/en not_active Expired
- 1976-04-30 CA CA251,589A patent/CA1070711A/fr not_active Expired
- 1976-05-01 JP JP4941676A patent/JPS51133212A/ja active Pending
- 1976-05-03 BE BE166686A patent/BE841409A/fr unknown
- 1976-05-03 FR FR7613115A patent/FR2310331A1/fr active Granted

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4550185A (en) *	1983-12-22	1985-10-29	E. I. Du Pont De Nemours And Company	Process for making tetrahydrofuran and 1,4-butanediol using Pd/Re hydrogenation catalyst
US4609636A (en) *	1983-12-22	1986-09-02	E. I. Du Pont De Nemours And Company	Pd/Re hydrogenation catalyst for making tetrahydrofuran and 1,4-butanediol
US7935834B2 (en)	2004-07-01	2011-05-03	Isp Investments Inc.	Catalysts for maleic acid hydrogenation to 1,4-butanediol
US8188320B2 (en)	2009-01-28	2012-05-29	Basf Se	Process for preparing pure cyclododecanone
CN110396072A (zh) *	2019-09-02	2019-11-01	上海欣海国际贸易有限公司	(s)-3-羟基四氢呋喃的制备方法
CN110396072B (zh) *	2019-09-02	2022-09-13	上海欣海健伟实业有限公司	(s)-3-羟基四氢呋喃的制备方法

Also Published As

Publication number	Publication date
NL7604539A (nl)	1976-11-05
GB1551741A (en)	1979-08-30
DE2519817A1 (de)	1976-11-11
BE841409A (fr)	1976-11-03
JPS51133212A (en)	1976-11-18
FR2310331A1 (fr)	1976-12-03
FR2310331B1 (fr)	1980-05-09

Legal Events

Date	Code	Title	Description
1997-01-29	MKEX	Expiry

Publication	Publication Date	Title
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