JPS601297B2 - 脂肪族第三アミンの製造方法 - Google Patents
脂肪族第三アミンの製造方法Info
- Publication number
- JPS601297B2 JPS601297B2 JP51092851A JP9285176A JPS601297B2 JP S601297 B2 JPS601297 B2 JP S601297B2 JP 51092851 A JP51092851 A JP 51092851A JP 9285176 A JP9285176 A JP 9285176A JP S601297 B2 JPS601297 B2 JP S601297B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- hydrogen
- amine
- gas
- alcohol
- Prior art date
- 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
Links
- -1 aliphatic tertiary amine Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 74
- 239000007789 gas Substances 0.000 claims description 56
- 150000001412 amines Chemical class 0.000 claims description 46
- 239000003054 catalyst Substances 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 21
- 150000001298 alcohols Chemical class 0.000 claims description 12
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000010941 cobalt Substances 0.000 claims description 8
- 229910017052 cobalt Inorganic materials 0.000 claims description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 8
- 239000002912 waste gas Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000008246 gaseous mixture Substances 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- 150000003512 tertiary amines Chemical class 0.000 description 23
- 150000001299 aldehydes Chemical class 0.000 description 18
- 239000006227 byproduct Substances 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 11
- 150000003141 primary amines Chemical class 0.000 description 10
- 150000003335 secondary amines Chemical class 0.000 description 10
- VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical group CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 238000007098 aminolysis reaction Methods 0.000 description 7
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 5
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 229940089454 lauryl aldehyde Drugs 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- ATBNMWWDBWBAHM-UHFFFAOYSA-N n-decyl-n-methyldecan-1-amine Chemical compound CCCCCCCCCCN(C)CCCCCCCCCC ATBNMWWDBWBAHM-UHFFFAOYSA-N 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 2
- 235000003642 hunger Nutrition 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- IKVDMBQGHZVMRN-UHFFFAOYSA-N n-methyldecan-1-amine Chemical compound CCCCCCCCCCNC IKVDMBQGHZVMRN-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000037351 starvation Effects 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- VBCJJAZGEJSVTL-UHFFFAOYSA-N (Z)-18-methylnonadec-9-en-1-amine Chemical compound CC(CCCCCCCC=C/CCCCCCCCN)C VBCJJAZGEJSVTL-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- DRHABPMHZRIRAH-UHFFFAOYSA-N 2,4,4,6,6-pentamethylhept-2-ene Chemical group CC(C)=CC(C)(C)CC(C)(C)C DRHABPMHZRIRAH-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- 241000206761 Bacillariophyta Species 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KYSNMMBYIQXAGN-UHFFFAOYSA-N [Co+2].[Cu+2].[O-][Cr]([O-])=O.[O-][Cr]([O-])=O Chemical compound [Co+2].[Cu+2].[O-][Cr]([O-])=O.[O-][Cr]([O-])=O KYSNMMBYIQXAGN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- YGNZEXMLVCBCQY-UHFFFAOYSA-N n,n,11-trimethyldodecan-1-amine Chemical compound CC(C)CCCCCCCCCCN(C)C YGNZEXMLVCBCQY-UHFFFAOYSA-N 0.000 description 1
- AIVGHALKDNEHNX-UHFFFAOYSA-N n,n,6-trimethylheptan-1-amine Chemical compound CC(C)CCCCCN(C)C AIVGHALKDNEHNX-UHFFFAOYSA-N 0.000 description 1
- VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 229940045681 other alkylating agent in atc Drugs 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/18—Stationary reactors having moving elements inside
- B01J19/1868—Stationary reactors having moving elements inside resulting in a loop-type movement
- B01J19/1881—Stationary reactors having moving elements inside resulting in a loop-type movement externally, i.e. the mixture leaving the vessel and subsequently re-entering it
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00094—Jackets
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00103—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor in a heat exchanger separate from the reactor
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00105—Controlling the temperature by indirect heating or cooling employing heat exchange fluids part or all of the reactants being heated or cooled outside the reactor while recycling
- B01J2219/00108—Controlling the temperature by indirect heating or cooling employing heat exchange fluids part or all of the reactants being heated or cooled outside the reactor while recycling involving reactant vapours
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2535073A DE2535073C3 (de) | 1975-08-06 | 1975-08-06 | Verfahren zur Herstellung von tertiären aliphatischen Aminen |
| DE2535073.6 | 1975-08-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5219604A JPS5219604A (en) | 1977-02-15 |
| JPS601297B2 true JPS601297B2 (ja) | 1985-01-14 |
Family
ID=5953342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51092851A Expired JPS601297B2 (ja) | 1975-08-06 | 1976-08-05 | 脂肪族第三アミンの製造方法 |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS601297B2 (enExample) |
| AR (1) | AR208045A1 (enExample) |
| AT (1) | AT346823B (enExample) |
| AU (1) | AU509878B2 (enExample) |
| BE (1) | BE844974A (enExample) |
| BR (1) | BR7605125A (enExample) |
| CA (1) | CA1101889A (enExample) |
| CH (1) | CH622237A5 (enExample) |
| DD (1) | DD125657A5 (enExample) |
| DE (1) | DE2535073C3 (enExample) |
| DK (1) | DK145493C (enExample) |
| ES (1) | ES450344A1 (enExample) |
| FI (1) | FI62822C (enExample) |
| FR (1) | FR2320287A1 (enExample) |
| GB (1) | GB1538138A (enExample) |
| HU (1) | HU178244B (enExample) |
| IE (1) | IE43613B1 (enExample) |
| IT (1) | IT1065117B (enExample) |
| LU (1) | LU75536A1 (enExample) |
| MX (1) | MX143899A (enExample) |
| NL (1) | NL186765C (enExample) |
| NO (1) | NO142709C (enExample) |
| PL (1) | PL106214B1 (enExample) |
| PT (1) | PT65443B (enExample) |
| SE (1) | SE433207B (enExample) |
| SU (1) | SU745359A3 (enExample) |
| YU (1) | YU193476A (enExample) |
| ZA (1) | ZA764757B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2621449C3 (de) * | 1976-05-14 | 1988-07-07 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von tertiären Aminen |
| DE2639648A1 (de) * | 1976-09-03 | 1978-03-16 | Basf Ag | Verfahren zur herstellung von tertiaeren aminen |
| BE530219A (enExample) * | 1976-05-14 | |||
| BE871092A (nl) * | 1977-10-17 | 1979-04-09 | Shell Int Research | Werkwijze ter bereiding van een amine |
| DE2824908A1 (de) * | 1978-06-07 | 1979-12-20 | Basf Ag | Verfahren zur herstellung von omega, omega'-bis-dialkylaminoalkanen |
| JPS559019A (en) * | 1978-07-04 | 1980-01-22 | Lion Corp | Preparation of tertiary long-chain aliphatic methylamine |
| DE3060282D1 (en) * | 1979-08-14 | 1982-05-19 | Ugine Kuhlmann | Process for the preparation of dimethylethyl amine |
| FR2463120A1 (fr) * | 1979-08-14 | 1981-02-20 | Ugine Kuhlmann | Procede de preparation de la dimethylethylamine |
| US4255357A (en) * | 1980-03-24 | 1981-03-10 | Pennwalt Corporation | Catalytic process for preparing ethyl amines |
| JPS59106441A (ja) * | 1982-12-09 | 1984-06-20 | New Japan Chem Co Ltd | 脂肪族第３アミンの製造方法 |
| JPS6115865A (ja) * | 1984-06-29 | 1986-01-23 | Kao Corp | 第３級アミンの製造方法 |
| DE3539266A1 (de) * | 1985-11-06 | 1987-05-07 | Basf Ag | Verfahren zur herstellung von trialkylaminen |
| DE3942793A1 (de) * | 1989-12-23 | 1991-06-27 | Hoechst Ag | Verfahren zur herstellung von n,n-dimethylaminen |
| JP2706595B2 (ja) * | 1991-04-22 | 1998-01-28 | 花王株式会社 | Ｎ−アルキルもしくはアルケニル−ｎ−メチルアミンの製造方法 |
| JP5750367B2 (ja) * | 2010-12-27 | 2015-07-22 | 花王株式会社 | ３級アミンの製造方法 |
| PH12013501363A1 (en) * | 2010-12-27 | 2013-08-28 | Kao Corp | Tertiary amine preparation process |
| JP5879123B2 (ja) * | 2011-12-27 | 2016-03-08 | 花王株式会社 | ３級アミンの製造方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE500692C (de) * | 1925-05-24 | 1930-09-05 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von reinem Eisen |
| US2597701A (en) * | 1948-12-06 | 1952-05-20 | Gen Aniline & Film Corp | Method of producing finely divided metals |
| DE824198C (de) * | 1949-10-22 | 1951-12-10 | Basf Ag | Verfahren zur Herstellung von Eisenpulver |
| DE833955C (de) * | 1950-01-03 | 1952-03-13 | Basf Ag | Herstellung von grobkoernigen Metallpulvern |
| US2612440A (en) * | 1950-05-03 | 1952-09-30 | Gen Aniline & Film Corp | Production of metal carbonyl powders of small size |
| US2674528A (en) * | 1951-01-22 | 1954-04-06 | Gen Aniline & Film Corp | Production of metal carbonyl powders of small size |
| DE936391C (de) * | 1954-01-06 | 1955-12-29 | Basf Ag | Verfahren zur Herstellung von Metallpulvern |
| GB825740A (en) * | 1957-01-24 | 1959-12-23 | Gen Aniline & Film Corp | Production of finely divided metals |
| DE1433361A1 (de) * | 1964-11-26 | 1968-12-12 | Friedenberg Serafima E | Verfahren zur Herstellung von hochdispersem Karbonyleisenpulver |
-
1975
- 1975-08-06 DE DE2535073A patent/DE2535073C3/de not_active Expired
-
1976
- 1976-01-01 AR AR264239A patent/AR208045A1/es active
- 1976-07-30 NL NLAANVRAGE7608493,A patent/NL186765C/xx not_active IP Right Cessation
- 1976-07-31 ES ES450344A patent/ES450344A1/es not_active Expired
- 1976-08-03 CH CH990876A patent/CH622237A5/de not_active IP Right Cessation
- 1976-08-04 DD DD194209A patent/DD125657A5/xx unknown
- 1976-08-04 SE SE7608741A patent/SE433207B/xx unknown
- 1976-08-04 FI FI762223A patent/FI62822C/fi not_active IP Right Cessation
- 1976-08-04 AT AT574976A patent/AT346823B/de not_active IP Right Cessation
- 1976-08-04 LU LU75536A patent/LU75536A1/xx unknown
- 1976-08-04 IT IT26035/76A patent/IT1065117B/it active
- 1976-08-04 HU HU76HO1920A patent/HU178244B/hu unknown
- 1976-08-05 YU YU01934/76A patent/YU193476A/xx unknown
- 1976-08-05 NO NO762730A patent/NO142709C/no unknown
- 1976-08-05 PT PT65443A patent/PT65443B/pt unknown
- 1976-08-05 BR BR7605125A patent/BR7605125A/pt unknown
- 1976-08-05 PL PL1976191645A patent/PL106214B1/pl unknown
- 1976-08-05 CA CA258,464A patent/CA1101889A/en not_active Expired
- 1976-08-05 AU AU16582/76A patent/AU509878B2/en not_active Expired
- 1976-08-05 DK DK353976A patent/DK145493C/da active
- 1976-08-05 IE IE1729/76A patent/IE43613B1/en unknown
- 1976-08-05 MX MX165794A patent/MX143899A/es unknown
- 1976-08-05 SU SU762388321A patent/SU745359A3/ru active
- 1976-08-05 JP JP51092851A patent/JPS601297B2/ja not_active Expired
- 1976-08-06 FR FR7624063A patent/FR2320287A1/fr active Granted
- 1976-08-06 BE BE169632A patent/BE844974A/xx not_active IP Right Cessation
- 1976-08-06 ZA ZA764757A patent/ZA764757B/xx unknown
- 1976-08-06 GB GB32873/76A patent/GB1538138A/en not_active Expired
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