JP4944440B2 - 脂環式カルボン酸またはその誘導体の製法 - Google Patents
脂環式カルボン酸またはその誘導体の製法 Download PDFInfo
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- JP4944440B2 JP4944440B2 JP2005379458A JP2005379458A JP4944440B2 JP 4944440 B2 JP4944440 B2 JP 4944440B2 JP 2005379458 A JP2005379458 A JP 2005379458A JP 2005379458 A JP2005379458 A JP 2005379458A JP 4944440 B2 JP4944440 B2 JP 4944440B2
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- -1 alicyclic carboxylic acid Chemical class 0.000 title claims description 39
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 132
- 238000000034 method Methods 0.000 claims description 64
- 150000002148 esters Chemical class 0.000 claims description 59
- 239000002253 acid Substances 0.000 claims description 36
- 239000003054 catalyst Substances 0.000 claims description 31
- 239000007789 gas Substances 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 150000007513 acids Chemical class 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 230000000737 periodic effect Effects 0.000 claims description 6
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- VUHMHACHBVTPMF-UHFFFAOYSA-N nonyl benzoate Chemical compound CCCCCCCCCOC(=O)C1=CC=CC=C1 VUHMHACHBVTPMF-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 239000011949 solid catalyst Substances 0.000 claims description 3
- 239000004408 titanium dioxide Substances 0.000 claims description 3
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- RLPSARLYTKXVSE-UHFFFAOYSA-N 1-(1,3-thiazol-5-yl)ethanamine Chemical compound CC(N)C1=CN=CS1 RLPSARLYTKXVSE-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 57
- 239000000047 product Substances 0.000 description 21
- 239000007788 liquid Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 11
- 125000002723 alicyclic group Chemical group 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 238000007037 hydroformylation reaction Methods 0.000 description 9
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 9
- 239000004033 plastic Substances 0.000 description 9
- 229920003023 plastic Polymers 0.000 description 9
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 8
- 239000007791 liquid phase Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 6
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 6
- 102100035474 DNA polymerase kappa Human genes 0.000 description 5
- 101710108091 DNA polymerase kappa Proteins 0.000 description 5
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
- 238000005882 aldol condensation reaction Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000005498 phthalate group Chemical class 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical class CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- 239000004808 2-ethylhexylester Substances 0.000 description 2
- REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- GCAIEATUVJFSMC-UHFFFAOYSA-N benzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1C(O)=O GCAIEATUVJFSMC-UHFFFAOYSA-N 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 238000005555 metalworking Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
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- BJQHLKABXJIVAM-BGYRXZFFSA-N 1-o-[(2r)-2-ethylhexyl] 2-o-[(2s)-2-ethylhexyl] benzene-1,2-dicarboxylate Chemical compound CCCC[C@H](CC)COC(=O)C1=CC=CC=C1C(=O)OC[C@H](CC)CCCC BJQHLKABXJIVAM-BGYRXZFFSA-N 0.000 description 1
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- AENMERKUOIIQIS-UHFFFAOYSA-N 3,4-bis(8-methylnonyl)phthalic acid;didecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCC.CC(C)CCCCCCCC1=CC=C(C(O)=O)C(C(O)=O)=C1CCCCCCCC(C)C AENMERKUOIIQIS-UHFFFAOYSA-N 0.000 description 1
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- HNDYULRADYGBDU-UHFFFAOYSA-N 8-methylnonyl benzoate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1 HNDYULRADYGBDU-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- GODULZVBAZDXQS-UHFFFAOYSA-N C(CC)C(CO)CCCCC.C(CCCC)=O Chemical compound C(CC)C(CO)CCCCC.C(CCCC)=O GODULZVBAZDXQS-UHFFFAOYSA-N 0.000 description 1
- ZPOLMKYSZXRCKE-UHFFFAOYSA-N C(CCCCCCC(C)C)OC(C1=CC=C(C(=O)OCCCCCCCC(C)C)C=C1)=O.C(CCCCCCCCC)OC(C1=CC=C(C(=O)OCCCCCCCCCC)C=C1)=O Chemical compound C(CCCCCCC(C)C)OC(C1=CC=C(C(=O)OCCCCCCCC(C)C)C=C1)=O.C(CCCCCCCCC)OC(C1=CC=C(C(=O)OCCCCCCCCCC)C=C1)=O ZPOLMKYSZXRCKE-UHFFFAOYSA-N 0.000 description 1
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- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- 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
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Description
US5286898およびUS5319129には、ジメチルテレフタレートをNi、Ptおよび/またはRuがドープされている、Pd−担持触媒上で、140℃以上の温度および50〜170バールの圧力で水素化して相応するヘキサヒドロジメチルテレフタレートに変換することができる方法が記載されている。
および物質交換のための高い界面が存在するように調節する。
a)ジ−またはポリカルボン酸を完全エステルおよび部分エステルが同時に存在するようにアルコールで部分エステル化する。
b)すくなことも2種のカルボン酸の混合物をアルコールでエステル化し、その際少なくとも2種の完全エステルの混合物が生じる。
c)ジ−またはポリカルボン酸をアルコール混合物と反応させ、その際相応する完全エステルの混合物を製造することができる。
d)ジ−またはポリカルボン酸をアルコール混合物で平行してエステル化する。
e)少なくとも2種のカルボン酸の混合物をアルコール混合物で部分的にエステル化する。
f)少なくとも2種のジ−またはポリカルボン酸からなる混合物をアルコール混合物で部分エステル化する。
線状ブテンからヒドロホルミル化および引き続く水素化により製造されたC5−アルコール混合物;
イソブテンまたは線状ブテンとイソブテンとを含有するブテン混合物からヒドロホルミル化および引き続く水素化により製造されたC5−アルコール混合物;
ペンテンまたは2種以上のペンテンの混合物からヒドロホルミル化および引き続く水素化により製造されたC6−アルコール混合物;
トリエチレンまたはジプロペンまたはヘキセン異性体またはヘキセン異性体のその他の混合物からヒドロホルミル化および引き続く水素化により製造されたC7−アルコール混合物;
n−ブチルアルデヒドのアルドール縮合および引き続く水素化により製造された2−エチルヘキサノール(2種の異性体)のような、C8−アルコール混合物;
C4−オレフィンから二量体化、ヒドロホルミル化および水素化により製造されたC9−アルコール混合物。この際、C9−アルコールを製造するためには、イソブテンから、または線状ブテンの混合物から、または線状ブテンとイソブテンとの混合物から出発することができる。C4−オレフィンを種々異なる触媒、例えば、プロトン酸、ゼオライト、有機金属のニッケル化合物またはニッケル含有接触触媒を用いて二量体化することができる。C8−オレフィン混合物のヒドロホルミル化はロジウム−またはコバルト触媒を用いて実施することができる。従って、多数の工業用C9−アルコール混合物が存在する。
トリプロピレンからヒドロホルミル化および引き続く水素化により製造されたC10−アルコール混合物;バレルアルデヒドのアルドール縮合および引き続く水素化により製造された2−プロピルヘプタノール(2種の異性体);
少なくとも2種のC5−アルデヒドの混合物から、アルドール縮合および引き続く水素化により製造されたC10−アルコール混合物;
ジヘキセン、ヘキサエチレン、テトラプロピレンまたはトリブテンからヒドロホルミル化および引き続く水素化により製造されたC13−アルコール混合物
である。
エステル基の酸素原子に結合する炭素原子4〜8個を有する同一または異なるアルキル基、特にn−ブチル基、n−ヘキシル基、n−オクチル基および2−エチルヘキシル基およびイソノニル基を有するポリアクリレート、ポリメタクリレート、ポリメチルメタクリレート、メチルアクリレート−ブチルアクリレート−コポリマー、メチルメタクリレート−ブチルメタクリレート−コポリマー、エチレン−酢酸ビニル−コポリマー、塩素化ポリエチレン、ニトリルゴム、アクリロニトリル−ブタジエン−スチレン−コポリマー、エチレン−プロピレン−コポリマー、エチレン−プロピレン−ジエン−コポリマー、スチレン−アクリロニトリル−コポリマー、アクリロニトリル−ブタジエン−ゴム、スチレン−ブタジエン−エラストマー、メチルメタクリレート−スチレン−ブタジエン−コポリマーおよび/またはニトロセルロース。
ホース、ケーブル、ワイヤ被覆材、絶縁テープ、自動車両および家具構造体において、プラスチゾル、フロアーの被覆材料において、医療製品、食品包装材料、シール、フィルム、複合フィルム、プレート、人工皮革、おもちゃ、壁紙、包装容器、粘着テープフィルム、衣料、被覆剤、繊維の被覆剤、靴、アンダーコーティング、シームシーリング、モデリングコンパウンドまたはボール。
水素化反応器は管型反応器であり、これを選択的に直通路式でまたはループ式で連続的に運転した。全ての実験において、液相および水素化ガスを並流で上方から下方に流した。
水素化を3工程で実施した。最初の2つの工程においては、反応器をループ式でおよび第3の工程において直通路式で運転した。運転パラメータおよび実施例1の質量流量を第1表にまとめた。
第1の反応器:9.54 l/h
第2の反応器:9.592 l/h
第3の反応器:9.643 l/h
第1表に示したLHSVを保持して、前記体積流のためには次の触媒量が生じる:
第1の反応器:1.35 l
第2の反応器:4.07 l
第3の反応器:12.36 l。
水素化を2つの工程で実施した。第1の工程では反応器をループ式で運転し、第2の工程では直通路式で運転した。
Claims (18)
- 脂環式カルボン酸またはその誘導体を、相応する芳香族カルボン酸またはその誘導体を固定床中に設けられた固体触媒上で、水素含有ガスで接触水素化することにより連続的に製造する方法において、水素化を少なくとも3つの直列接続する水素化ユニット中で実施し、少なくとも最初の2つの直列接続する水素化ユニットをループ式で運転し、ループ式で運転する少なくとも2つの水素化ユニットを異なる滞留時間で運転し、この際、ループ式で運転する水素化ユニットの一方における滞留時間が、直接後接するループ式で運転する水素化ユニットにおけるより短いことを特徴とする、脂環式カルボン酸またはその誘導体の連続的製法。
- 全ての水素化ユニットをループ式で運転する、請求項1記載の製法。
- 最後の水素化ユニットを直通路式で運転する、請求項1記載の製法。
- 水素化を3つより多数の水素化ユニットを有する装置中で実施する、請求項1から3までのいずれか1項記載の製法。
- 水素化を、3つの水素化ユニットを有する装置中で実施する、請求項1から3までのいずれか1項記載の製法。
- 元素の周期系の第8副族の金属少なくとも1種を含有する触媒を使用する、請求項1から5までのいずれか1項記載の製法。
- ルテニウムを含有する触媒を使用する、請求項6記載の製法。
- 二酸化チタン−担体を有する触媒を使用する、請求項1から7までのいずれか1項記載の製法。
- 芳香族カルボン酸またはその誘導体として、モノ−、ジ−またはポリカルボン酸またはその誘導体を使用する請求項1から8までのいずれか1項記載の製法。
- 芳香族ジ−またはポリカルボン酸またはその誘導体として、ベンゼン−、ジフェニル−、ナフタレン−、ジフェニルオキシド−またはアントラセン−ジ−またはポリカルボン酸、その無水物および/またはその相応するエステルを使用する、請求項1から9までのいずれか1項記載の製法。
- 芳香族モノカルボン酸として、安息香酸、1−ナフトエ酸または2−ナフトエ酸、その無水物またはそのエステルを使用する、請求項9記載の製法。
- 芳香族カルボン酸誘導体としてカルボン酸エステルを使用する、請求項1から11までのいずれか1項記載の製法。
- ジ−またはポリカルボン酸誘導体の使用において、部分エステルおよび/または完全エステルを使用する、請求項12記載の製法。
- 使用する芳香族カルボン酸エステルのアルコール成分が、炭素原子1〜25個を有する分枝または非分枝のアルコキシアルキル基、シクロアルキル基および/またはアルキル基を有する請求項12または13記載の製法。
- 使用する芳香族ジ−および/またはポリカルボン酸エステルのアルコール成分がそれぞれ同一または異なっている、請求項12から14までのいずれか1項記載の製法。
- 芳香族ジカルボン酸誘導体としてジイソノニルフタレートまたはジデシルフタレートを使用する請求項9から14までのいずれか1項記載の製法。
- 芳香族モノカルボン酸誘導体として、イソノニルベンゾエートまたはデシルベンゾエートを使用する、請求項11記載の製法。
- 連続するループ型反応器中の滞留時間の比が0.01〜1未満である、請求項1から17までのいずれか1項記載の製法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102004063637.0 | 2004-12-31 | ||
DE102004063637A DE102004063637A1 (de) | 2004-12-31 | 2004-12-31 | Verfahren zur Herstellung von alicyclischen Carbonsäuren oder deren Derivaten |
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JP2006188521A JP2006188521A (ja) | 2006-07-20 |
JP4944440B2 true JP4944440B2 (ja) | 2012-05-30 |
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JP2005379458A Active JP4944440B2 (ja) | 2004-12-31 | 2005-12-28 | 脂環式カルボン酸またはその誘導体の製法 |
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US (1) | US7435848B2 (ja) |
EP (1) | EP1676828B1 (ja) |
JP (1) | JP4944440B2 (ja) |
CN (1) | CN100537508C (ja) |
DE (2) | DE102004063637A1 (ja) |
ES (1) | ES2330233T3 (ja) |
SG (1) | SG123729A1 (ja) |
TW (1) | TWI359808B (ja) |
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DE102004063637A1 (de) | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von alicyclischen Carbonsäuren oder deren Derivaten |
DE102005028752A1 (de) | 2005-06-22 | 2007-01-04 | Oxeno Olefinchemie Gmbh | Gemisch von Diisononylestern der 1,2-Cyclohexandicarbonsäure, Verfahren zu deren Herstellung und Verwendung dieser Gemische |
DE102006001795A1 (de) * | 2006-01-12 | 2007-07-19 | Oxeno Olefinchemie Gmbh | Terephthalsäuredialkylester und deren Verwendung |
DE102006026624A1 (de) * | 2006-06-08 | 2007-12-13 | Oxeno Olefinchemie Gmbh | Tripentylcitrate und deren Verwendung |
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JP2018500273A (ja) * | 2014-10-29 | 2018-01-11 | エクソンモービル ケミカル パテンツ インコーポレイテッド | ベンゼンポリカルボン酸およびその誘導体の水素化のための改善された方法 |
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ES2814342T3 (es) | 2017-07-05 | 2021-03-26 | Basf Se | Hidrogenación de compuestos aromáticos |
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DE10347863A1 (de) * | 2003-10-10 | 2005-05-04 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Benzoesäureestern |
DE102004063637A1 (de) | 2004-12-31 | 2006-07-13 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von alicyclischen Carbonsäuren oder deren Derivaten |
-
2004
- 2004-12-31 DE DE102004063637A patent/DE102004063637A1/de not_active Ceased
-
2005
- 2005-11-03 DE DE502005007836T patent/DE502005007836D1/de active Active
- 2005-11-03 EP EP05110309A patent/EP1676828B1/de active Active
- 2005-11-03 ES ES05110309T patent/ES2330233T3/es active Active
- 2005-12-15 SG SG200508114A patent/SG123729A1/en unknown
- 2005-12-26 TW TW094146523A patent/TWI359808B/zh active
- 2005-12-28 JP JP2005379458A patent/JP4944440B2/ja active Active
- 2005-12-30 CN CNB200510137580XA patent/CN100537508C/zh not_active Expired - Fee Related
-
2006
- 2006-01-03 US US11/322,349 patent/US7435848B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
ES2330233T3 (es) | 2009-12-07 |
EP1676828B1 (de) | 2009-08-05 |
EP1676828A3 (de) | 2008-04-09 |
CN100537508C (zh) | 2009-09-09 |
SG123729A1 (en) | 2006-07-26 |
JP2006188521A (ja) | 2006-07-20 |
DE102004063637A1 (de) | 2006-07-13 |
EP1676828A2 (de) | 2006-07-05 |
TWI359808B (en) | 2012-03-11 |
DE502005007836D1 (de) | 2009-09-17 |
US20060167151A1 (en) | 2006-07-27 |
US7435848B2 (en) | 2008-10-14 |
CN1796353A (zh) | 2006-07-05 |
TW200640852A (en) | 2006-12-01 |
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