JPH0550497B2 - - Google Patents

Info

Publication number: JPH0550497B2
Authority: JP; Japan
Prior art keywords: serine; reaction; gal; hydrolysis; cyanoamination
Prior art date: 1984-06-25
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 - Lifetime

Application number

JP12927084A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6110542A (ja

Inventor

Sadao Kitagawa

Takashi Yokoi

Mitsumasa Minafuji

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.)

KEISHITSU RYUBUN SHINYOTO

KEISHITSU RYUBUN SHINYOTO KAIHATSU GIJUTSU KENKYU KUMIAI

Original Assignee

KEISHITSU RYUBUN SHINYOTO

KEISHITSU RYUBUN SHINYOTO KAIHATSU GIJUTSU KENKYU KUMIAI

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.)

1984-06-25

Filing date

1984-06-25

Publication date

1993-07-29

1984-06-25 Application filed by KEISHITSU RYUBUN SHINYOTO, KEISHITSU RYUBUN SHINYOTO KAIHATSU GIJUTSU KENKYU KUMIAI filed Critical KEISHITSU RYUBUN SHINYOTO

1984-06-25 Priority to JP12927084A priority Critical patent/JPS6110542A/ja

1986-01-18 Publication of JPS6110542A publication Critical patent/JPS6110542A/ja

1993-07-29 Publication of JPH0550497B2 publication Critical patent/JPH0550497B2/ja

Status Granted legal-status Critical Current

Links

MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 41
238000006460 hydrolysis reaction Methods 0.000 claims description 25
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
230000007062 hydrolysis Effects 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 12
239000011541 reaction mixture Substances 0.000 claims description 10
229910021529 ammonia Inorganic materials 0.000 claims description 9
WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 45
238000006243 chemical reaction Methods 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
150000001298 alcohols Chemical class 0.000 description 16
238000000034 method Methods 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000047 product Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
239000002994 raw material Substances 0.000 description 7
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
235000019270 ammonium chloride Nutrition 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
230000003301 hydrolyzing effect Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
229910052921 ammonium sulfate Inorganic materials 0.000 description 3
235000011130 ammonium sulphate Nutrition 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000002955 isolation Methods 0.000 description 3
238000000746 purification Methods 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000001099 ammonium carbonate Substances 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
-1 nitrile compound Chemical class 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ZRXHLJNBNWVNIM-UHFFFAOYSA-N 3-methyl-1-benzofuran Chemical compound C1=CC=C2C(C)=COC2=C1 ZRXHLJNBNWVNIM-UHFFFAOYSA-N 0.000 description 1
229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
CWVZGJORVTZXFW-UHFFFAOYSA-N [benzyl(dimethyl)silyl]methyl carbamate Chemical compound NC(=O)OC[Si](C)(C)CC1=CC=CC=C1 CWVZGJORVTZXFW-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
150000001370 alpha-amino acid derivatives Chemical group 0.000 description 1
235000008206 alpha-amino acids Nutrition 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
235000012538 ammonium bicarbonate Nutrition 0.000 description 1
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000490 cosmetic additive Substances 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
229960003067 cystine Drugs 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
FKWSMBAMOQCVPV-UHFFFAOYSA-N magnesium dicyanide Chemical compound [Mg+2].N#[C-].N#[C-] FKWSMBAMOQCVPV-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP12927084A 1984-06-25 1984-06-25 セリンの製造法 Granted JPS6110542A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP12927084A JPS6110542A (ja)	1984-06-25	1984-06-25	セリンの製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP12927084A JPS6110542A (ja)	1984-06-25	1984-06-25	セリンの製造法

Publications (2)

Publication Number	Publication Date
JPS6110542A JPS6110542A (ja)	1986-01-18
JPH0550497B2 true JPH0550497B2 (de)	1993-07-29

Family

ID=15005428

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP12927084A Granted JPS6110542A (ja)	1984-06-25	1984-06-25	セリンの製造法

Country Status (1)

Country	Link
JP (1)	JPS6110542A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH02174752A (ja) *	1988-12-27	1990-07-06	Res Assoc Util Of Light Oil	Ｄｌ―セリンの製造方法
DE68921722T2 (de) *	1988-12-27	1995-09-07	Mitsubishi Chem Corp	Verfahren zur Herstellung von DL-Serin, und Verfahren zu dessen Trennung und Reinigung.

1984
- 1984-06-25 JP JP12927084A patent/JPS6110542A/ja active Granted

Also Published As

Publication number	Publication date
JPS6110542A (ja)	1986-01-18

Publication	Publication Date	Title
GB1575469A (en)	1980-09-24	Recovery of glycine and iminodiacetic acid
JPH0550497B2 (de)	1993-07-29
CN1208311C (zh)	2005-06-29	制备亚烷基二胺三乙酸的方法
JP3874820B2 (ja)	2007-01-31	タウリン類縁体の製造方法
US3131210A (en)	1964-04-28	Process for methionine nitrile synthesis
US3009954A (en)	1961-11-21	Process for the production of sarcosine and related alkylamino-acetic acids
WO1996001802A1 (en)	1996-01-25	A process for obtaining [s,s]-ethylenediamine-n,n'-disuccinic acid from a salt solution of such acid and l-aspartic acid
JPS5945670B2 (ja)	1984-11-07	γ−アミノ−β−ヒドロキシ酪酸の製法
US3748355A (en)	1973-07-24	Crystallization process for the recovery of alkaline nitrilotriacetates
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US4028406A (en)	1977-06-07	Process of preparing penicillamine
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KR800001550B1 (ko)	1980-12-27	5-(4-히드록시페닐) 히단토인의 제조법
US20230008538A1 (en)	2023-01-12	Process for preparing nitrile intermediates for nitrogen-containing chelators
US3211784A (en)	1965-10-12	Method of preparing alpha-amino-beta-hydroxybutyric acid
FI66836C (fi)	1984-12-10	Foerfarande foer framstaellning av fast natrium- eller kalium-p-hydroximandelatmonohydrat
JPS6337105B2 (de)	1988-07-22
JPS6120539B2 (de)	1986-05-22
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