NO134467B - - Google Patents
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- Publication number
- NO134467B NO134467B NO4827/72A NO482772A NO134467B NO 134467 B NO134467 B NO 134467B NO 4827/72 A NO4827/72 A NO 4827/72A NO 482772 A NO482772 A NO 482772A NO 134467 B NO134467 B NO 134467B
- Authority
- NO
- Norway
- Prior art keywords
- alcohol
- reactor
- ester
- column
- acid
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
- 150000002148 esters Chemical class 0.000 claims description 24
- 238000004821 distillation Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 12
- 230000032050 esterification Effects 0.000 claims description 10
- 238000005886 esterification reaction Methods 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000010924 continuous production Methods 0.000 claims description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 6
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 5
- 229960001826 dimethylphthalate Drugs 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000004508 fractional distillation Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/914—Transfer or decalcomania
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31801—Of wax or waxy material
- Y10T428/31804—Next to cellulosic
- Y10T428/31808—Cellulosic is paper
- Y10T428/31812—Glassine paper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Color Printing (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB6073071A GB1416867A (en) | 1971-12-30 | 1971-12-30 | Colour formers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134467B true NO134467B (da) | 1976-07-05 |
| NO134467C NO134467C (da) | 1976-10-13 |
Family
ID=10485987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4827/72A NO134467C (da) | 1971-12-30 | 1972-12-29 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3963853A (da) |
| JP (1) | JPS572515B2 (da) |
| AR (1) | AR196506A1 (da) |
| BE (1) | BE793585A (da) |
| BR (1) | BR7209212D0 (da) |
| CA (1) | CA971963A (da) |
| CH (1) | CH569020A5 (da) |
| DE (1) | DE2264033A1 (da) |
| DK (1) | DK142168B (da) |
| ES (1) | ES410108A1 (da) |
| FI (1) | FI54714C (da) |
| FR (1) | FR2169893B1 (da) |
| GB (1) | GB1416867A (da) |
| IN (1) | IN138495B (da) |
| IT (1) | IT976337B (da) |
| NL (1) | NL163248B (da) |
| NO (1) | NO134467C (da) |
| SE (1) | SE396719B (da) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4143891A (en) * | 1976-12-29 | 1979-03-13 | Transkirt Corporation | Negotiable document |
| DE3218646A1 (de) * | 1982-05-18 | 1983-11-24 | Hoechst Ag, 6230 Frankfurt | Fluoranverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbbildner in kopiersystemen |
| US5224897A (en) * | 1989-04-06 | 1993-07-06 | Linden Gerald E | Self-replicating duplex forms |
| US5248279A (en) * | 1989-04-06 | 1993-09-28 | Linden Gerald E | Two-sided, self-replicating forms |
| US5135437A (en) * | 1989-11-13 | 1992-08-04 | Schubert Keith E | Form for making two-sided carbonless copies of information entered on both sides of an original sheet and methods of making and using same |
| US5137494A (en) * | 1989-11-13 | 1992-08-11 | Schubert Keith E | Two-sided forms and methods of laying out, printing and filling out same |
| US5127879A (en) * | 1989-04-06 | 1992-07-07 | Schubert Keith E | Apparatus for recordkeeping |
| US5154668A (en) * | 1989-04-06 | 1992-10-13 | Schubert Keith E | Single paper sheet forming a two-sided copy of information entered on both sides thereof |
| US5395288A (en) * | 1989-04-06 | 1995-03-07 | Linden; Gerald E. | Two-way-write type, single sheet, self-replicating forms |
| US6280322B1 (en) | 1989-11-13 | 2001-08-28 | Gerald E. Linden | Single sheet of paper for duplicating information entered on both surfaces thereof |
| JPH0520485U (ja) * | 1991-08-22 | 1993-03-12 | 株式会社富士通ゼネラル | リモートコントロール装置 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3432327A (en) * | 1964-03-13 | 1969-03-11 | Pilot Pen Co Ltd | Pressure sensitive copying sheet and the production thereof |
| US3427180A (en) * | 1965-03-31 | 1969-02-11 | Ncr Co | Pressure-sensitive record system and compositions |
| US3764369A (en) * | 1969-01-21 | 1973-10-09 | Ncr | Pressure sensitive recording unit |
| US3769302A (en) * | 1969-01-21 | 1973-10-30 | T Hoover | Aliphatic amino-substituted flourans |
| US3825561A (en) * | 1970-10-12 | 1974-07-23 | Sumitomo Chemical Co | Fluoran compounds |
| JPS4838158A (da) * | 1971-09-14 | 1973-06-05 | ||
| US3736279A (en) * | 1972-04-03 | 1973-05-29 | Ford Motor Co | Stable nonaqueous compositions capable of forming thermosetting films |
| JPS4921609A (da) * | 1972-06-23 | 1974-02-26 | ||
| JPS553155A (en) * | 1978-06-22 | 1980-01-10 | Mitsubishi Electric Corp | Safety device for discharge lamp |
-
1971
- 1971-12-30 GB GB6073071A patent/GB1416867A/en not_active Expired
-
1972
- 1972-12-21 FI FI3634/72A patent/FI54714C/fi active
- 1972-12-22 IN IN2216/1972A patent/IN138495B/en unknown
- 1972-12-27 US US05/318,774 patent/US3963853A/en not_active Expired - Lifetime
- 1972-12-28 BR BR9212/72A patent/BR7209212D0/pt unknown
- 1972-12-28 ES ES410108A patent/ES410108A1/es not_active Expired
- 1972-12-29 DK DK654572AA patent/DK142168B/da not_active IP Right Cessation
- 1972-12-29 FR FR7246937A patent/FR2169893B1/fr not_active Expired
- 1972-12-29 CA CA160,289A patent/CA971963A/en not_active Expired
- 1972-12-29 NO NO4827/72A patent/NO134467C/no unknown
- 1972-12-29 SE SE7217179A patent/SE396719B/xx unknown
- 1972-12-29 CH CH1903772A patent/CH569020A5/xx not_active IP Right Cessation
- 1972-12-29 BE BE793585D patent/BE793585A/xx not_active IP Right Cessation
- 1972-12-29 IT IT71269/72A patent/IT976337B/it active
- 1972-12-29 NL NL7217809.A patent/NL163248B/xx not_active IP Right Cessation
- 1972-12-29 AR AR245947A patent/AR196506A1/es active
- 1972-12-29 DE DE2264033A patent/DE2264033A1/de active Pending
- 1972-12-30 JP JP734258A patent/JPS572515B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE396719B (sv) | 1977-10-03 |
| CA971963A (en) | 1975-07-29 |
| FI54714B (fi) | 1978-10-31 |
| BE793585A (fr) | 1973-06-29 |
| NO134467C (da) | 1976-10-13 |
| GB1416867A (en) | 1975-12-10 |
| FI54714C (fi) | 1979-02-12 |
| FR2169893A1 (da) | 1973-09-14 |
| CH569020A5 (da) | 1975-11-14 |
| AR196506A1 (es) | 1974-02-06 |
| NL7217809A (da) | 1973-07-03 |
| NL163248B (nl) | 1980-03-17 |
| JPS4874312A (da) | 1973-10-06 |
| JPS572515B2 (da) | 1982-01-16 |
| IT976337B (it) | 1974-08-20 |
| ES410108A1 (es) | 1976-03-16 |
| BR7209212D0 (pt) | 1973-09-13 |
| IN138495B (da) | 1976-02-14 |
| US3963853A (en) | 1976-06-15 |
| DK142168B (da) | 1980-09-15 |
| DE2264033A1 (de) | 1973-07-05 |
| FR2169893B1 (da) | 1977-09-02 |
| DK142168C (da) | 1981-02-16 |
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